5-n-Butylindan-1-one oxime → 5-n-Butylindan-1-ylamine

HRID 19717Notes

Reaction equation

HRID 19717 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[N:14]O)[CH2:9][CH2:8]2)[CH2:2][CH2:3][CH3:4]>C(O)(=O)C.[Pd]>[CH2:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH:10]([NH2:14])[CH2:9][CH2:8]2)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 860040385-n-Butylindan-1-one oxime

Product 1

HCID 685606235-n-Butylindan-1-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 5-n-butylindan-1-one oxime (0.50 g, 2.46 mmol) and 10% Pd/C (0.50 g) in acetic acid (50 ml) is hydrogenated at 3.5 bar for 16 hours. The reaction is filtered through a Celite™ filter pad and partitioned between ether and water. The organic phase is washed with saturated NaHCO3 then brine and dried (MgSO4). Evaporation affords the title compound. NMR δH 0.85 (t J 7.3 3H), 1.26 (sextet J 7.3 2H), 1.50 (quintet J 7.3 2H), 1.58 (m 1H), 2.10 (br s 1H), 2.40 (m 1H), 2.50 (t J 8.0 2H), 2.70 (m 1H), 2.88 (m 1H), 4.38 (t J 6 1H), 6.95 (m 3H), 7.16 (d J 8.3 2H)

Workup

  1. filtrationThe reaction is filtered through a Celite™
  2. filtrationfilter pad
  3. custompartitioned between ether and water
  4. washThe organic phase is washed with saturated NaHCO3
  5. dry with materialbrine and dried (MgSO4)
  6. customEvaporation

Sources & evidence

ORD record
ord-d853827dadec43ef8cf694049f004e55
Source dataset
uspto-grants-2010_06
Patent number
US07745462B2

Reaction notes

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